Penn Entertainment Fined $25,000 Over Barstool Sportsbook Promo

10.01.2025

Penn Sports Interactive (PSI), the sports betting arm of Penn Entertainment, received a $25,000 fine from the Massachusetts Gaming Commission (MGC). The penalty arose from a misleading promotion tied to the Barstool Sportsbook, which Penn replaced with ESPN Bet in late 2023.

What Went Wrong: “Big Cat’s Can’t Lose Parlay”

The fine, first pointed out by Jessica Welman of SBC Americas, addressed a promotion called “Big Cat’s Can’t Lose Parlay.” According to the MGC, the name suggested the bet was risk-free. This language violated regulations designed to protect consumers, especially those unfamiliar with sports betting.

The Commission identified two specific violations:

  1. G.L. c. 23N, §4(c): Prohibits deceptive or misleading advertising that creates false impressions.
  2. 205 CMR 256.04(6)(c): Forbids promotions implying that a bet is “risk-free” unless it complies with strict disclosure requirements.

While Penn Sports Interactive ceased offering the “Can’t Lose Parlay” in Massachusetts after the issue was raised, the MGC found that the promotion still violated state rules. The Commission emphasized that the language used in sports betting advertisements must not mislead or create ambiguous expectations among consumers.

Mitigating Factors and Penalty

Penn responded by quickly discontinuing the “Can’t Lose Parlay” in Massachusetts. The MGC acknowledged this action as a sign of good faith. However, the Commission maintained that the misleading language warranted a penalty.

Officials emphasized the importance of transparency in advertising to protect consumers.

The End of Barstool Sportsbook

At the time of the violation, the Barstool Sportsbook brand was the operational platform in Massachusetts under a partnership between Penn Entertainment and Barstool Sports. However, Penn rebranded its sports betting operations in November 2023, launching ESPN Bet after ending its relationship with Barstool Sports.

The fine serves as a reminder of the regulatory scrutiny operators face, especially during a period of transition for Penn Entertainment’s sports betting ventures. With the launch of ESPN Bet, the company is positioning itself under a globally recognized brand, which brings both opportunities and heightened expectations for compliance.